maraviroc Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals CCR5 (Chemokine CC motif receptor 5) receptor antagonists 1635 376348-65-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • MD6P741W8A
  • UK-427857
  • maravirok
  • marawirok
  • maraviroc
  • celsentri
  • selzentry
Maraviroc is a member of a therapeutic class called CCR5 co-receptor antagonists. Maraviroc selectively binds to the human chemokine receptor CCR5 present on the cell membrane, preventing the interaction of HIV-1 gp120 and CCR5 necessary for CCR5-tropic HIV-1 to enter cells. CXCR4-tropic and dual-tropic HIV-1 entry is not inhibited by maraviroc.
  • Molecular weight: 513.68
  • Formula: C29H41F2N5O
  • CLOGP: 3.26
  • LIPINSKI: 1
  • HAC: 6
  • HDO: 1
  • TPSA: 63.05
  • ALOGS: -4.68
  • ROTB: 8

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.60 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 8 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 33.37 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 23 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.25 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 12.80 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 6, 2007 FDA VIIV HLTHCARE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Exposure during pregnancy 67.05 41.21 33 705 108179 46577145
Abortion spontaneous 65.85 41.21 25 713 43621 46641703
Pathogen resistance 61.05 41.21 15 723 6045 46679279
CSF test abnormal 50.38 41.21 8 730 337 46684987
Generalised anxiety disorder 49.52 41.21 10 728 1650 46683674
Live birth 48.61 41.21 14 724 10316 46675008
Viral mutation identified 48.18 41.21 10 728 1889 46683435
Social avoidant behaviour 44.18 41.21 10 728 2829 46682495
Hyperbilirubinaemia 44.05 41.21 13 725 10425 46674899

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Virologic failure 141.97 23.80 35 2070 3184 29947189
Viral mutation identified 107.97 23.80 27 2078 2599 29947774
Immune reconstitution inflammatory syndrome 63.77 23.80 24 2081 9077 29941296
Progressive multifocal leukoencephalopathy 46.33 23.80 19 2086 8994 29941379
Drug resistance 45.48 23.80 24 2081 20109 29930264
Pathogen resistance 44.16 23.80 18 2087 8392 29941981
Viral load increased 41.47 23.80 13 2092 2841 29947532
Lipodystrophy acquired 38.65 23.80 13 2092 3547 29946826
Enanthema 37.19 23.80 8 2097 395 29949978
CSF HIV escape syndrome 33.37 23.80 6 2099 115 29950258
Blood HIV RNULL increased 31.66 23.80 9 2096 1407 29948966
Anal cancer 31.00 23.80 7 2098 433 29949940
Hodgkin's disease 30.52 23.80 8 2097 924 29949449
Drug interaction 30.51 23.80 52 2053 199516 29750857
Congenital renal disorder 29.09 23.80 5 2100 73 29950300
Congenital ureteric anomaly 27.82 23.80 4 2101 16 29950357
Kidney enlargement 27.01 23.80 7 2098 773 29949600
Congenital vesicoureteric reflux 25.94 23.80 4 2101 28 29950345
Acquired immunodeficiency syndrome 24.72 23.80 6 2099 508 29949865

Pharmacologic Action:

SourceCodeDescription
ATC J05AX09 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Other antivirals
FDA MoA N0000175445 Chemokine Co-receptor 5 Antagonists
FDA EPC N0000175572 CCR5 Co-receptor Antagonist
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D065100 CCR5 Receptor Antagonists
MeSH PA D023581 HIV Fusion Inhibitors
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:59886 hiv entry inhibitors
CHEBI has role CHEBI:63673 chemokine receptor 5 antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
CCR5 Tropic Drug Resistant HIV Infection indication
Myocardial infarction contraindication 22298006 DOID:5844
Orthostatic hypotension contraindication 28651003
Infectious disease contraindication 40733004
Viral hepatitis C contraindication 50711007 DOID:1883
Acute nephropathy contraindication 58574008
Chronic type B viral hepatitis contraindication 61977001
Chronic renal failure syndrome contraindication 90688005
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.8 Basic
pKa2 5.07 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
20MG/ML SELZENTRY VIIV HLTHCARE N208984 Nov. 4, 2016 RX SOLUTION ORAL Oct. 30, 2023 NEW PATIENT POPULATION
20MG/ML SELZENTRY VIIV HLTHCARE N208984 Nov. 4, 2016 RX SOLUTION ORAL April 30, 2024 PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
C-C chemokine receptor type 5 GPCR ANTAGONIST Kd 7.60 CHEMBL CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 4.76 CHEMBL
C-C chemokine receptor type 5 GPCR Ki 9.62 CHEMBL

External reference:

IDSource
4026629 VUID
N0000179791 NUI
D06670 KEGG_DRUG
4026629 VANDF
C1964465 UMLSCUI
CHEBI:63608 CHEBI
CHEMBL1201187 ChEMBL_ID
D000077592 MESH_DESCRIPTOR_UI
DB04835 DRUGBANK_ID
3002977 PUBCHEM_CID
806 IUPHAR_LIGAND_ID
8450 INN_ID
MD6P741W8A UNII
620216 RXNORM
118030 MMSL
24072 MMSL
d06852 MMSL
012282 NDDF
427805000 SNOMEDCT_US
429603001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
SELZENTRY HUMAN PRESCRIPTION DRUG LABEL 1 49702-223 TABLET, FILM COATED 150 mg ORAL NDA 31 sections
SELZENTRY HUMAN PRESCRIPTION DRUG LABEL 1 49702-224 TABLET, FILM COATED 300 mg ORAL NDA 31 sections
SELZENTRY HUMAN PRESCRIPTION DRUG LABEL 1 49702-233 TABLET, FILM COATED 25 mg ORAL NDA 31 sections
SELZENTRY HUMAN PRESCRIPTION DRUG LABEL 1 49702-235 TABLET, FILM COATED 75 mg ORAL NDA 31 sections
SELZENTRY HUMAN PRESCRIPTION DRUG LABEL 1 49702-237 SOLUTION 20 mg ORAL NDA 31 sections
SELZENTRY HUMAN PRESCRIPTION DRUG LABEL 1 54868-5809 TABLET, FILM COATED 300 mg ORAL NDA 32 sections